data_D01
# 
_chem_comp.id                                    D01 
_chem_comp.name                                  "2-({4-[(5-CHLORO-1H-INDOL-2-YL)SULFONYL]PIPERAZIN-1-YL}CARBONYL)THIENO[3,2-B]PYRIDINE 4-OXIDE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H17 Cl N4 O4 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "2-[[4-[(5-CHLOROINDOL-2-YL)SULFONYL]PIPERAZIN-1-YL] CARBONYL]THIENO[3,2-B]PYRIDINE N-OXIDE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-08-26 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        476.956 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     D01 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        2D1J 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
# 
loop_
_chem_comp_atom.comp_id 
_chem_comp_atom.atom_id 
_chem_comp_atom.alt_atom_id 
_chem_comp_atom.type_symbol 
_chem_comp_atom.charge 
_chem_comp_atom.pdbx_align 
_chem_comp_atom.pdbx_aromatic_flag 
_chem_comp_atom.pdbx_leaving_atom_flag 
_chem_comp_atom.pdbx_stereo_config 
_chem_comp_atom.model_Cartn_x 
_chem_comp_atom.model_Cartn_y 
_chem_comp_atom.model_Cartn_z 
_chem_comp_atom.pdbx_model_Cartn_x_ideal 
_chem_comp_atom.pdbx_model_Cartn_y_ideal 
_chem_comp_atom.pdbx_model_Cartn_z_ideal 
_chem_comp_atom.pdbx_component_atom_id 
_chem_comp_atom.pdbx_component_comp_id 
_chem_comp_atom.pdbx_ordinal 
D01 N1   N1   N  0  1 Y N N 8.247  8.582  25.676 -3.615 0.050  -1.464 N1   D01 1  
D01 C1   C1   C  0  1 Y N N 9.541  8.286  26.094 -4.706 0.777  -1.040 C1   D01 2  
D01 C2   C2   C  0  1 Y N N 10.012 7.616  27.178 -5.376 1.883  -1.554 C2   D01 3  
D01 C3   C3   C  0  1 Y N N 11.401 7.461  27.324 -6.464 2.398  -0.885 C3   D01 4  
D01 C4   C4   C  0  1 Y N N 12.280 8.011  26.391 -6.904 1.825  0.301  C4   D01 5  
D01 CL1  CL1  CL 0  0 N N N 13.989 7.815  26.643 -8.278 2.492  1.125  CL1  D01 6  
D01 C5   C5   C  0  1 Y N N 11.804 8.729  25.304 -6.255 0.729  0.827  C5   D01 7  
D01 C6   C6   C  0  1 Y N N 10.447 8.858  25.133 -5.150 0.196  0.161  C6   D01 8  
D01 C7   C7   C  0  1 Y N N 9.636  9.498  24.108 -4.252 -0.932 0.422  C7   D01 9  
D01 C8   C8   C  0  1 Y N N 8.350  9.272  24.540 -3.358 -0.961 -0.580 C8   D01 10 
D01 S1   S1   S  0  1 N N N 6.882  9.746  23.868 -2.053 -2.134 -0.735 S1   D01 11 
D01 O1   O1   O  0  1 N N N 5.995  9.999  24.999 -2.451 -3.260 0.034  O1   D01 12 
D01 O2   O2   O  0  1 N N N 7.138  10.714 22.835 -1.718 -2.158 -2.116 O2   D01 13 
D01 N2   N2   N  0  1 N N N 6.239  8.348  23.088 -0.729 -1.507 0.037  N2   D01 14 
D01 C9   C9   C  0  1 N N N 7.055  7.734  22.052 -0.498 -1.775 1.464  C9   D01 15 
D01 C10  C10  C  0  1 N N N 6.145  7.009  21.069 0.899  -2.385 1.628  C10  D01 16 
D01 N3   N3   N  0  1 N N N 5.269  6.058  21.755 1.865  -1.550 0.899  N3   D01 17 
D01 C11  C11  C  0  1 N N N 5.387  4.701  21.638 2.942  -1.039 1.528  C11  D01 18 
D01 O3   O3   O  0  1 N N N 4.844  4.000  22.493 3.052  -1.152 2.734  O3   D01 19 
D01 C12  C12  C  0  1 Y N N 6.158  4.061  20.670 3.984  -0.346 0.755  C12  D01 20 
D01 C13  C13  C  0  1 Y N N 6.014  3.891  19.279 4.927  0.528  1.198  C13  D01 21 
D01 C14  C14  C  0  1 Y N N 7.100  3.163  18.700 5.847  1.086  0.293  C14  D01 22 
D01 C15  C15  C  0  1 Y N N 8.083  2.774  19.660 5.696  0.678  -1.052 C15  D01 23 
D01 S2   S2   S  0  1 Y N N 7.618  3.327  21.172 4.322  -0.444 -0.994 S2   D01 24 
D01 C16  C16  C  0  1 Y N N 9.207  2.030  19.190 6.523  1.145  -2.054 C16  D01 25 
D01 C17  C17  C  0  1 Y N N 9.363  1.704  17.866 7.520  2.043  -1.708 C17  D01 26 
D01 C18  C18  C  0  1 Y N N 8.376  2.101  17.007 7.635  2.425  -0.378 C18  D01 27 
D01 N4   N4   N  1  1 Y N N 7.314  2.761  17.400 6.839  1.968  0.553  N4   D01 28 
D01 O4   O4   O  -1 1 N N N 6.453  3.063  16.467 7.026  2.409  1.886  O4   D01 29 
D01 C19  C19  C  0  1 N N N 4.611  6.529  22.980 1.631  -1.277 -0.526 C19  D01 30 
D01 C20  C20  C  0  1 N N N 5.587  7.304  23.887 0.236  -0.672 -0.691 C20  D01 31 
D01 HN1  HN1  H  0  1 N N N 7.399  8.325  26.140 -3.106 0.228  -2.270 HN1  D01 32 
D01 H2   H2   H  0  1 N N N 9.332  7.211  27.913 -5.042 2.337  -2.475 H2   D01 33 
D01 H3   H3   H  0  1 N N N 11.792 6.911  28.167 -6.981 3.257  -1.287 H3   D01 34 
D01 H5   H5   H  0  1 N N N 12.490 9.180  24.602 -6.599 0.286  1.750  H5   D01 35 
D01 H7   H7   H  0  1 N N N 9.964  10.023 23.223 -4.299 -1.610 1.261  H7   D01 36 
D01 H91  1H9  H  0  1 N N N 7.626  8.511  21.523 -1.249 -2.476 1.830  H91  D01 37 
D01 H92  2H9  H  0  1 N N N 7.756  7.018  22.507 -0.559 -0.843 2.026  H92  D01 38 
D01 H101 1H10 H  0  0 N N N 5.524  7.751  20.546 0.908  -3.395 1.219  H101 D01 39 
D01 H102 2H10 H  0  0 N N N 6.774  6.452  20.359 1.164  -2.413 2.685  H102 D01 40 
D01 H13  H13  H  0  1 N N N 5.176  4.269  18.712 4.971  0.790  2.245  H13  D01 41 
D01 H16  H16  H  0  1 N N N 9.958  1.714  19.899 6.397  0.821  -3.076 H16  D01 42 
D01 H17  H17  H  0  1 N N N 10.227 1.158  17.518 8.191  2.437  -2.456 H17  D01 43 
D01 H18  H18  H  0  1 N N N 8.476  1.860  15.959 8.410  3.125  -0.103 H18  D01 44 
D01 H191 1H19 H  0  0 N N N 3.781  7.196  22.702 2.380  -0.575 -0.893 H191 D01 45 
D01 H192 2H19 H  0  0 N N N 4.247  5.652  23.535 1.694  -2.209 -1.087 H192 D01 46 
D01 H201 1H20 H  0  0 N N N 6.345  6.617  24.291 -0.029 -0.644 -1.748 H201 D01 47 
D01 H202 2H20 H  0  0 N N N 5.039  7.760  24.725 0.228  0.339  -0.283 H202 D01 48 
# 
loop_
_chem_comp_bond.comp_id 
_chem_comp_bond.atom_id_1 
_chem_comp_bond.atom_id_2 
_chem_comp_bond.value_order 
_chem_comp_bond.pdbx_aromatic_flag 
_chem_comp_bond.pdbx_stereo_config 
_chem_comp_bond.pdbx_ordinal 
D01 N1  C1   SING Y N 1  
D01 N1  C8   SING Y N 2  
D01 N1  HN1  SING N N 3  
D01 C1  C2   DOUB Y N 4  
D01 C1  C6   SING Y N 5  
D01 C2  C3   SING Y N 6  
D01 C2  H2   SING N N 7  
D01 C3  C4   DOUB Y N 8  
D01 C3  H3   SING N N 9  
D01 C4  CL1  SING N N 10 
D01 C4  C5   SING Y N 11 
D01 C5  C6   DOUB Y N 12 
D01 C5  H5   SING N N 13 
D01 C6  C7   SING Y N 14 
D01 C7  C8   DOUB Y N 15 
D01 C7  H7   SING N N 16 
D01 C8  S1   SING N N 17 
D01 S1  O1   DOUB N N 18 
D01 S1  O2   DOUB N N 19 
D01 S1  N2   SING N N 20 
D01 N2  C9   SING N N 21 
D01 N2  C20  SING N N 22 
D01 C9  C10  SING N N 23 
D01 C9  H91  SING N N 24 
D01 C9  H92  SING N N 25 
D01 C10 N3   SING N N 26 
D01 C10 H101 SING N N 27 
D01 C10 H102 SING N N 28 
D01 N3  C11  SING N N 29 
D01 N3  C19  SING N N 30 
D01 C11 O3   DOUB N N 31 
D01 C11 C12  SING N N 32 
D01 C12 C13  DOUB Y N 33 
D01 C12 S2   SING Y N 34 
D01 C13 C14  SING Y N 35 
D01 C13 H13  SING N N 36 
D01 C14 C15  DOUB Y N 37 
D01 C14 N4   SING Y N 38 
D01 C15 S2   SING Y N 39 
D01 C15 C16  SING Y N 40 
D01 C16 C17  DOUB Y N 41 
D01 C16 H16  SING N N 42 
D01 C17 C18  SING Y N 43 
D01 C17 H17  SING N N 44 
D01 C18 N4   DOUB Y N 45 
D01 C18 H18  SING N N 46 
D01 N4  O4   SING N N 47 
D01 C19 C20  SING N N 48 
D01 C19 H191 SING N N 49 
D01 C19 H192 SING N N 50 
D01 C20 H201 SING N N 51 
D01 C20 H202 SING N N 52 
# 
loop_
_pdbx_chem_comp_descriptor.comp_id 
_pdbx_chem_comp_descriptor.type 
_pdbx_chem_comp_descriptor.program 
_pdbx_chem_comp_descriptor.program_version 
_pdbx_chem_comp_descriptor.descriptor 
D01 SMILES           ACDLabs              10.04 Clc1cc2cc(nc2cc1)S(=O)(=O)N5CCN(C(=O)c4sc3ccc[n+]([O-])c3c4)CC5                                                                                 
D01 InChI            InChI                1.02b InChI=1/C20H17ClN4O4S2/c21-14-3-4-15-13(10-14)11-19(22-15)31(28,29)24-8-6-23(7-9-24)20(26)18-12-16-17(30-18)2-1-5-25(16)27/h1-5,10-12,22H,6-9H2 
D01 InChIKey         InChI                1.02b DHDQMXPAANQKDC-UHFFFAOYAO                                                                                                                       
D01 SMILES_CANONICAL CACTVS               3.341 [O-][n+]1cccc2sc(cc12)C(=O)N3CCN(CC3)[S](=O)(=O)c4[nH]c5ccc(Cl)cc5c4                                                                            
D01 SMILES           CACTVS               3.341 [O-][n+]1cccc2sc(cc12)C(=O)N3CCN(CC3)[S](=O)(=O)c4[nH]c5ccc(Cl)cc5c4                                                                            
D01 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc2c(cc(s2)C(=O)N3CCN(CC3)S(=O)(=O)c4cc5cc(ccc5[nH]4)Cl)[n+](c1)[O-]                                                                          
D01 SMILES           "OpenEye OEToolkits" 1.5.0 c1cc2c(cc(s2)C(=O)N3CCN(CC3)S(=O)(=O)c4cc5cc(ccc5[nH]4)Cl)[n+](c1)[O-]                                                                          
# 
loop_
_pdbx_chem_comp_identifier.comp_id 
_pdbx_chem_comp_identifier.type 
_pdbx_chem_comp_identifier.program 
_pdbx_chem_comp_identifier.program_version 
_pdbx_chem_comp_identifier.identifier 
D01 "SYSTEMATIC NAME" ACDLabs              10.04 "2-({4-[(5-chloro-1H-indol-2-yl)sulfonyl]piperazin-1-yl}carbonyl)thieno[3,2-b]pyridine 4-oxide"        
D01 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 [4-[(5-chloro-1H-indol-2-yl)sulfonyl]piperazin-1-yl]-(4-oxidothieno[4,5-b]pyridin-4-ium-2-yl)methanone 
# 
